Substituted thiene-3-ylsulphonylamino(thio)carbonyl-triazolin(thi)ones

ABSTRACT

The invention relates to novel substituted thiene-3-ylsulphonylamino(thio)carbonyl-triazolin(ethi)ones of the formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which Q 1 , Q 2 , R 1 , R 2 , R 3  and R 4  are as defined in the disclosure, except for prior-art compounds. 
           
         
       
    
     The invention further relates to the preparation of the compounds, to their use as herbicides, and to herbicidal compositions comprising the novel compounds.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP02/11743, filed Oct. 21, 2002, whichwas published in German as International Patent Publication WO 03/037086on May 8, 2003, which is entitled to the right of priority of GermanPatent Application 101 54 074.4, filed Nov. 2, 2001.

The invention relates to novel substitutedthiene-3-ylsulphonylamino(thio)carbonyl-triazolin(ethi)ones, toprocesses for their preparation and to their use as herbicides.

It is already known that certain substitutedthienylsulphonylamino(thio)carbonyltriazolin(ethi)ones, such as, forexample, the compounds methyl4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-5-oxo-3-isopropoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,ethyl4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)thioxocarbonyl]amino]sulfonyl]-5-fluoro-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-thioxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-trifluoromethyl-3-thiophenecarboxylate,ethyl4-[[[(4,5-dihydro-4-ethyl-3-methoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylateand isopropyl4-[[[(3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)carbonyl]amino] sulfonyl]-5-ethyl-3-thiophenecarboxylate, have herbicidalproperties (cf WO-A-01/05788, cf also WO-A-97/16449, WO-A-98/24787).However, the activity of these compounds is not entirely satisfactory.

This invention now provides the novel substitutedthiene-3-ylsulphonylamino(thio)-carbonyltriazolin(ethi)ones of thegeneral formula (I)

in which

-   Q¹ represents O (oxygen) or S (sulphur),-   Q² represents O (oxygen) or S (sulphur),-   R¹ represents optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms,    represents in each case optionally cyano- or halogen-substituted    alkenyl or alkynyl having in each case 2 to 6 carbon atoms,    representing in each case optionally cyano-, halogen- or    C₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each    case 3 to 6 carbon atoms in the cycloalkyl group and, if    appropriate, 1 to 4 carbon atoms in the alkyl moiety, represents in    each case optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl- or    C₁-C₄-alkoxy-substituted aryl or arylalkyl having in each case 6 or    10 carbon atoms in the aryl group and, if appropriate, 1 to 4 carbon    atoms in the alkyl moiety, or represents in each case optionally    nitro-, cyano-, halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted    heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon    atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or    sulphur atoms in the heterocyclyl group and, if appropriate, 1 to 4    carbon atoms in the alkyl moiety,-   R² represents hydrogen, cyano, nitro, halogen, represents in each    case optionally, cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,    alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl    having in each case 1 to 6 carbon atoms in the alkyl group, or    represents in each case optionally cyano- or halogen-substituted    alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to    6 carbon atoms in the alkenyl or alkynyl group,-   R³ represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen,    represents optionally cyano-, halogen-, C₁-C₄-alkoxy-,    C₁-C₄-alkyl-carbonyl- or C₁-C₄-alkoxy-carbonyl-substituted alkyl    having 1 to 6 carbon atoms, represents in each case optionally    fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl    having in each case 2 to 6 carbon atoms, represents in each case    optionally cyano-, halogen-, C₁-C₄-alkoxy- or    C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or    alkylcarbonylamino having in each case 1 to 6 carbon atoms in the    alkyl group, represents alkenyloxy, alkynyloxy, alkenylthio,    alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6    carbon atoms in the alkenyl or alkynyl group, represents    dialkylamino having in each case 1 to 4 carbon atoms in the alkyl    groups, represents in each case optionally methyl- and/or    ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino,    represents in each case optionally fluorine-, chlorine-, bromine-,    cyano- and/or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkenyl,    cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl,    cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having    in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl    group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,    or represents in each case optionally fluorine-, chlorine-,    bromine-, cyano-, nitro-, C₁-C₄-alkyl-, trifluoromethyl-,    C₁-C₄-alkoxy- and/or C₁-C₄-alkoxy-carbonyl-substituted aryl,    arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino    or arylalkylamino having in each case 6 or 10 carbon atoms in the    aryl group and, if appropriate, 1 to 4 carbon atoms in the alkyl    moiety, and-   R⁴ represents hydrogen, hydroxy, amino, cyano, represents    C₂-C₁₀-alkylideneamino, represents optionally fluorine-, chlorine-,    bromine-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-alkyl-carbonyl- or    C₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms,    represents in each case optionally fluorine-, chlorine- and/or    bromine-substituted alkenyl or alkynyl having in each case 2 to 6    carbon atoms, represents in each case optionally fluorine-,    chlorine-, bromine-, cyano-, C₁-C₄-alkoxy- or    C₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylamino or    alkylcarbonylamino having in each case 1 to 6 carbon atoms in the    alkyl group, represents alkenyloxy having 3 to 6 carbon atoms,    represents dialkylamino having in each case 1 to 4 carbon atoms in    the alkyl groups, represents in each case optionally fluorine-,    chlorine-, bromine-, cyano- and/or C₁-C₄-alkyl-substituted    cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3    to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4    carbon atoms in the alkyl moiety, or represents in each case    optionally fluorine-, chlorine-, bromine-, cyano-, nitro-,    C₁-C₄-alkyl-, trifluoromethyl- and/or C₁-C₄-alkoxy-substituted aryl    or arylalkyl having in each case 6 or 10 carbon atoms in the aryl    group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,    or together with R³ represents optionally branched and/or    C₁-C₄-alkyl-substituted alkanediyl, oxaalkanediyl, thiaalkanediyl or    azaalkanediyl having 3 to 6 carbon atoms, where the oxa, thia or aza    components may be positioned at the beginning, at the end or within    the alkanediyl grouping,

—and salts of the compounds of the formula (I)—

except for the compounds methyl4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-5-oxo-3-isopropoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]-sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,ethyl4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)thioxocarbonyl]-amino]sulfonyl]-5-fluoro-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-thioxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-trifluoromethyl-3-thiophenecarboxylate,ethyl4-[[[(4,5-dihydro-4-ethyl-3-methoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylateand isopropyl4-[[[(3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-ethyl-3-thiophenecarboxylateknown from WO-A-01/05788, which are excluded by disclaimer.

Saturated or unsaturated hydrocarbon groupings, such as alkyl,allkanediyl, alkenyl or alkynyl, are in each case straight-chain orbranched as far as this is possible—including in combinations withheteroatoms, such as in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, and inthe case of polysubstitution, the substituents can be identical ordifferent.

Preferred substituents or ranges of the radicals present in the formulaelisted above and below are defined below.

-   Q¹ preferably represents O (oxygen) or S (sulphur).-   Q² preferably represents O (oxygen) or S (sulphur).-   R¹ preferably represents in each case optionally cyano-, fluorine-,    chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or    isoproyl, n-, iso-, s- or t-butyl, represents in each case    optionally cyano-, fluorine- or chlorine-substituted propenyl,    butenyl, propynyl or butynyl, represents in each case optionally    cyano-, fluorine-, chlorine-, methyl- or ethyl-substituted    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, represents    in each case optionally cyano-, fluorine-, chlorine-, methyl-,    ethyl-, n- or isopropyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or    isopropoxy-, difluoromethoxy- or trifluoromethoxy-substituted    phenyl, phenylmethyl or phenylethyl, or represents in each case    optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,    n- or isopropyl-, methoxy-, ethoxy-, n- or isopropoxy-substituted    heterocyclyl or heterocyclylmethyl, where the heterocyclyl group is    in each case selected from the group consisting of oxetanyl,    thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.-   R² preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, represents in each case optionally cyano-, fluorine-,    chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or    isopropyl, n-, iso-, s- or t-butyl, methoxy, ethoxy, n- or    isopropoxy, methoxycarbonyl, ethoxycarbonyl, n- or    isopropoxycarbonyl, methylthio, ethylthio, n- or isopropylthio,    methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or    represents in each case optionally cyano-, fluorine- or    chlorine-substituted propenyl, butenyl, propynyl, butynyl,    propenyloxy, butenyloxy, propynyloxy or butynyloxy.-   R³ preferably represents hydrogen, hydroxy, mercapto, amino, cyano,    fluorine, chlorine, bromine, represents in each case optionally    fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or isopropoxy-,    acetyl-, propionyl-, n- or isobutyroyl-, methoxycarbonyl-,    ethoxycarbonyl-, n- or isopropoxycarbonyl-substituted methyl, ethyl,    n- or isopropyl, n-, iso-, s- or t-butyl, n-, iso-, s- or t-pentyl    or neopentyl, represents in each case optionally fluorine-,    chlorine- and/or bromine-substituted ethenyl, propenyl, butenyl,    ethynyl, propynyl or butynyl, represents in each case optionally    fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or isopropoxy-,    n-, iso-, s- or t-butoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or    isopropoxycarbonyl-substituted methoxy, ethoxy, n- or isopropoxy,    n-, iso-, s- or t-butoxy, n-, iso-, s- or t-pentyloxy or    neopentyloxy, methylthio, ethylthio, n- or isopropylthio, n-, iso-,    s- or t-butylthio, methylamino, ethylamino, n- or isopropylamino,    n-, iso-, s- or t-butylamino, acetylamino or propionylamino,    represents propenyloxy, butenyloxy, ethynyloxy, propynyloxy,    butynyloxy, propenylthio, butenylthio, propynylthio, butynythio,    propenylamino, butenylamino, propynylamino or butynylamino,    represents dimethylamino, diethylamino or dipropylamino, represents    in each case optionally fluorine-, chlorine-, methyl- and/or    ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,    cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy,    cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,    cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino,    cyclopentylamino, cyclohexylamino, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,    cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,    cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio,    cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino,    cyclobutylmethylamino, cyclopentylmethylamino or    cyclohexylmethylamino, or represents in each case optionally    fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy-    or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy,    phenylthio, benzylthio, phenylamino or benzylamino.-   R⁴ preferably represents hydrogen, hydroxy, amino, represents in    each case optionally fluorine-, chlorine-, cyano-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s- or    t-butyl, represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl or    butynyl, represents in each case optionally fluorine-, chlorine-,    cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or    isopropoxy, n-, iso-, s- or t-butoxy, methylamino, ethylamino, n- or    isopropylamino, n-, iso-, s- or t-butylamino, represents propenyloxy    or butenyloxy, represents dimethylamino or diethylamino, represents    in each case optionally fluorine-, chlorine-, methyl- and/or    ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,    cyclopropylamino, cyclobutylamino, cyclopentylamino,    cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl,    cyclopentylmethyl or cyclohexylmethyl, or represents in each case    optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or    methoxy-substituted phenyl or benzyl.-   R³ and R⁴ together preferably represent trimethylene    (propane-1,3-diyl), 1-oxatrimethylene, 1-thiatrimethylene,    1-azatrimethylene, tetramethylene (butane-1,4-diyl),    1-oxatetramethylene, 1-thiatetramethylene, 1-azatetramethylene or    pentamethylene (pentane-1,5-diyl), each of which is optionally mono-    to trisubstituted by methyl and/or ethyl, where the position 1 is    connected to the point of attachment of R³.-   Q¹ particularly preferably represents O (oxygen) or S (sulphur).-   Q² particularly preferably represents O (oxygen) or S (sulphur).-   R¹ particularly preferably represents in each case optionally    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or isopropyl.-   R² particularly preferably represents fluorine, chlorine, bromine or    represents in each case optionally fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or isopropyl.-   R³ particularly preferably represents hydrogen, chlorine, bromine,    represents in each case optionally fluorine-, chlorine-, methoxy-,    ethoxy-, n- or isopropoxy-substituted methyl, ethyl, n- or    isopropyl, n-, iso-, s- or t-butyl, n-, iso-, s- or t-pentyl or    neopentyl, represents in each case optionally fluorine- or    chlorine-substituted ethenyl, propenyl, butenyl, propynyl or    butynyl, represents in each case optionally fluorine-, chlorine-,    methoxy-, ethoxy-, n- or isopropoxy-substituted methoxy, ethoxy, n-    or isopropoxy, n-, iso-, s- or t-butoxy, n-, iso-, s- or    t-pentyloxy, neopentyloxy, methylthio, ethylthio, n- or    isopropylthio, n-, iso-, s- or t-butylthio, methylamino, ethylamino,    n- or isopropylamino, represents propenyloxy, propynyloxy,    propenylthio, propynylthio, propenylamino or propynylamino,    represents dimethylamino or diethylamino, represents in each case    optionally fluorine-, chlorine- or methyl-substituted cyclopropyl,    cyclopropyloxy, cyclopropylmethyl, cyclopropylmethoxy,    cyclobutyloxy, cyclopentyloxy or cyclohexyloxy, or represents in    each case optionally fluorine-, chlorine- or methyl-substituted    phenoxy or benzyloxy.-   R⁴ particularly preferably represents in each case optionally    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or isopropyl, represents in each case optionally fluorine- or    chlorine-substituted ethenyl, propenyl or propynyl, represents in    each case optionally fluorine-, chlorine-, methoxy- or    ethoxy-substituted methoxy, ethoxy, n- or isopropoxy, represents    methylamino, or represents cyclopropyl.-   R³ and R⁴ together particularly preferably represent trimethylene    (propane-1,3-diyl), 1-oxatrimethylene, 1-thiatrimethylene,    1-azatrimethylene, tetramethylene (butane-1,4-diyl),    1-oxatetramethylene, 1-thiatetramethylene, 1-azatetramethylene or    pentamethylene (pentane-1,5-diyl), each of which is optionally mono-    or disubstituted by methyl, where the position 1 is connected to the    point of attachment of R³.

The invention preferably also provides the sodium, potassium, lithium,magnesium, calcium, ammonium, C₁-C₄-alkylammonium, (where the alkylradical is optionally substituted by hydroxyl), di(C₁-C₄-alkyl)ammonium,tri(C₁-C₄-alkyl)ammonium, tetra(C₁-C₄-alkyl)ammonium,tri(C₁-C₄-alkyl)sulfonium, C₅- or C₆-cycloalkylammonium anddi(C₁-C₂-alkyl)benzylammonium salt and also thedi(C₁-C₂-alkyl)pyridinylammonium salts and the pyrrolidinium salts ofcompounds of the formula (I) in which Q¹, Q², R¹, R², R³ and R⁴ have themeanings given above as being preferred.

A very particularly preferred group are those compounds of formula (I)in which

R¹ represents methyl and Q¹ and Q² and R², R³ and R⁴ have the meaningsgiven above as being particularly preferred,

except for the prior-art compounds methyl4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-5-oxo-3-isopropoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-3-methoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-3-ethoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thio-phenecarboxylate,methyl4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate,methyl4-[[[(4,5-dihydro-3-ethoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)thioxocarbonyl]amino]sulfonyl]-5-fluoro-3-thiophenecarboxylateand methyl4-[[[(4,5-dihydro-3-ethyl-4-methoxy-5-thioxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-trifluoromethyl-3-thio-phenecarboxylate.

A further very particularly preferred group are those compounds of theformula (I) in which

R¹ represents ethyl and Q¹ and Q² and R², R³ and R⁴ have the meaningsgiven above as being particularly preferred,

except for the prior-art compounds ethyl4-[[[(4,5-dihydro-3,4-dimethoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-chloro-3-thiophenecarboxylateand ethyl4-[[[(4,5-dihydro-4-ethyl-3-methoxy-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate.

A further very particularly preferred group are those compounds of theformula (I) in which

R¹ represents n-propyl and Q¹ and Q² and R², R³ and R⁴ have the meaningsgiven above as being particularly preferred.

A further very particularly preferred group are those compounds of theformula (I) in which

R¹ represents isopropyl and Q¹ and Q² and R², R³ and R⁴ have themeanings given above as being particularly preferred, except for theprior-art compound isopropyl4-[[[(3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-ethyl-3-thiophenecarboxylate.

A further very particularly preferred group are those compounds of theformula (I) in which

Q¹ and Q² and R¹ and R² have the meanings given above as beingparticularly preferred and R³ and R⁴ together represent trimethylene(propane-1,3-diyl), 1-oxatrimethylene, 1-thiatrimethylene,1-azatrimethylene, tetramethylene (butane-1,4-diyl),1-oxatetramethylene, 1-thiatetramethylene, 1-azatetramethylene orpentamethylene (pentane-1,5-diyl), each of which is optionally mono- ordisubstituted by methyl, where the position 1 is connected to the pointof attachment of R³.

Further groups which may be particularly emphasized are:

Group 1:

Compounds in which R³ represents halogen- or C₁-C₄-alkoxy-substitutedalkoxy having 1 to 6 carbon atoms.

Group 2:

Compounds in which R³ represents optionally methyl- and/orethyl-substituted cycloalkoxy having 3 to 6 carbon atoms.

Group 3:

Compounds in which R³ represents optionally fluorine-, chlorine-,bromine-, methyl-, trifluoromethyl-, methoxy- ormethoxycarbonyl-substituted phenoxy or benzyloxy.

The abovementioned general or preferred radical definitions apply bothto the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

Preference according to the invention is given to those compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

The novel substituted thien-3-yl sulphonylamino(thio)carbonyltriazolin(ethi)ones of the general formula (I) have interestingbiological properties. In particular, they have strong herbicidalactivity.

The novel substituted thien-3-yl sulphonylamino(thio)carbonyltriazolin(ethi)ones of the general formula (I) are obtained when

-   (a) substituted thiophene-3-sulphonamides of the general formula    (II)

in which

R¹ and R² are as defined above, are reacted with substitutedtriazolin(ethi)ones of the general formula (III)

in which

Q¹, Q², R³ and R⁴ are as defined above and

Z represents halogen, alkoxy, aryloxy or arylalkoxy,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

-   (b) substituted thien-3-yl sulphonyl iso(thio)cyanates of the    general formula (IV)

in which

Q¹, R¹ and R² are as defined above, are reacted with triazolin(ethi)onesof the general formula (V)

in which

Q², R⁴ and R⁵ are as defined above,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

-   (c) substituted thiophene-3-sulphonyl chlorides of the general    formula (VI)

in which

R¹ and R² are as defined above, are reacted with triazolin(ethi)ones ofthe general formula (V)

in which

Q², R⁴ and R⁵ are as defined above,

and metal (thio)cyanates of the general formula (VII)M-Q¹-CN   (VII)in which

Q¹ is as defined above,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

-   (d) substituted thiophene-3-sulphonyl chlorides of the general    formula (VI)

in which

R¹ and R² are as defined above, are reacted with triazolin(ethi)one(thio)carboxamides of the general formula (VIII)

in which

Q¹, Q², R³ and R⁴ are as defined above,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

or when

-   (e) substituted thien-3-yl sulphonylamino(thio)carbonyl compounds of    the general formula (IX)

in which

Q¹, R¹ and R² are as defined above and

Z represents halogen, alkoxy, aryloxy or arylalkoxy, are reacted withtriazolin(ethi)ones of the general formula (V)

in which

Q², R⁴ and R⁵ are each as defined above,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent,

and the compounds of the formula (I) obtained by the processes (a), (b),(c), (d) or (e) are, if appropriate, converted by customary methods intosalts.

Using, for example, 2-bromo-4-ethoxycarbonyl thiophene-3-sulphonamideand 4,5-dimethoxy-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-oneas starting materials, the course of the reaction in the process (a)according to the invention can be illustrated by the following formulascheme:

Using, for example, 2-dichloromethyl-4-methoxycarbonylthien-3-yl-sulphonyl iso-thiocyanate and5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one as startingmaterials, the course of the reaction in the process (b) according tothe invention can be illustrated by the following formula scheme:

Using, for example, 4-ethoxycarbonyl-2-ethyl thiophene-3-sulphonylchloride, 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazole-3-thione andpotassium cyanate as starting materials, the course of the reaction inthe process (c) according to the invention can be illustrated by thefollowing formula scheme:

Using, for example, 4-ethoxycarbonyl-2-trifluoromethylthiophene-3-sulphonyl chloride and 4-ethyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one-2-carboxamide as starting materials, the course ofthe reaction in the process (d) according to the invention can beillustrated by the following formula scheme:

Using, for example, O-methyl N-(2-ethyl-4-isopropoxycarbonylthien-3-yl-sulphonyl)urethane and4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials,the course of the reaction in the process (e) according to the inventioncan be illustrated by the following formula scheme:

The formula (II) provides a general definition of the substitutedthiophene-3-sulphonamides to be used as starting materials in theprocess (a) according to the invention for preparing compounds of thegeneral formula (I). In the general formula (II), R¹ and R² preferablyor in particular have those meanings which have already been mentionedabove, in connection with the description of the compounds of thegeneral formula (I) according to the invention, as being preferred orparticularly preferred for R¹ and R².

The substituted thiophene-3-sulphonamides of the general formula (II)are known and/or can be prepared by processes known per se (cf. J. Org.Chem. 45 (1980), 617-620, WO-A-01/05788).

The substituted thiophene-3-sulphonamides of the general formula (II)are obtained when substituted thiophene-3-sulphonyl chlorides of thegeneral formula (VI)

in which

R¹ and R² are as defined above, are reacted with ammonia or ammoniumsalts, such as, for example, ammonium acetate or ammonium carbonate, ifappropriate in the presence of a diluent, such as, for example, water ormethylene chloride, at temperatures between 0° C. and 100° C.

The formula (III) provides a general definition of the substitutedtriazolin(ethi)ones furthermore to be used as starting materials in theprocess (a) according to the invention for preparing compounds of thegeneral formula (I). In the general formula (III), Q¹, Q², R³ and R⁴preferably or in particular have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferredor particularly preferred for Q¹, Q², R³ and R⁴.

The starting materials of the general formula (III) are known and/or canbe prepared by processes known per se (cf. EP-A-341 489, EP-A-422 469,EP-A-425 948, EP-A-431 291, EP-A-507 171, EP-A-534 266).

The formula (IV) provides a general definition of the substitutedthien-3-yl sulphonyl iso(thio)cyanates to be used as starting materialsin the process (b) according to the invention for preparing compounds ofthe general formula (I). In the general formula (IV), Q¹, R¹ and R²preferably or in particular have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferredor particularly preferred for Q¹, R¹ and R².

The starting materials of the general formula (IV) are known and/or canbe prepared by processes known per se (cf. U.S. Pat. No.4,701,535).

The formula (V) provides a general definition of the triazolin(ethi)onesto be used as starting materials in the processes (b), (c) and (e)according to the invention for preparing compounds of the generalformula (I). In the general formula (V), Q², R⁴ and R⁵ preferably or inparticular have those meanings which have already been mentioned above,in connection with the description of the compounds of the generalformula (I) according to the invention, as being preferred orparticularly preferred for Q², R⁴ and R⁵.

The starting materials of the general formula (V) are known and/or canbe prepared by processes known per se (cf. EP-A-341 489, EP-A-422 469,EP-A-425 948, EP-A-431 291, EP-A-507 171, EP-A-534 266).

The formula (VI) provides a general definition of the substitutedthiophene-3-sulphonyl chlorides to be used as starting materials in theprocesses (c) and (d) according to the invention for preparing compoundsof the general formula (I). In the general formula (VI), R¹ and R²preferably or in particular have those meanings which have already beenmentioned above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferredor particularly preferred for R¹ and R².

The substituted thiophene-3-sulphonyl chlorides of the general formula(VI) are known and/or can be prepared by processes known per se (cf. J.Org. Chem. 45 (1980), 617-620, WO-A-01/05788).

The substituted thiophene-3-sulphonyl chlorides of the general formula(VI) are obtained when 3-amino-thiophene-4-carboxylic esters of thegeneral formula (X)

in which

R¹ and R² are as defined above,

—or acid adducts of compounds of the formula (X), such as, for example,the hydrochlorides—

are reacted with an alkali metal nitrite, such as, for example, sodiumnitrite, in the presence of hydrochloric acid at temperatures between−10° C. and +10° C., and the resulting diazonium salt solution isreacted with sulphur dioxide in the presence of a diluent, such as, forexample, dichloromethane, 1,2-dichloroethane or acetic acid, and in thepresence of a catalyst, such as, for example, copper(I) chloride and/orcopper(II) chloride, at temperatures between −10° C. and +50° C.

The intermediates of the general formula (X) are known and/or can beprepared by processes known per se (cf. Austr. J. Chem. 48 (1995),1907-1916; Preparation Examples).

The formula (VIII) provides a general definition of thetriazolin(ethi)one (thio)-carboxamides to be used as starting materialsin the process (d) according to the invention for preparing compounds ofthe general formula (I). In the general formula (VIII), Q¹, Q², R³ andR⁴ preferably or in particular have those meanings which have alreadybeen mentioned above, in connection with the description of thecompounds of the general formula (I) according to the invention, asbeing preferred or particularly preferred for Q¹, Q², R³ and R⁴.

The starting materials of the general formula (VIII) are known and/orcan be prepared by processes known per se.

The formula (IX) provides a general definition of the substitutedthien-3-yl-sulphonylamino(thio)carbonyl compounds to be used as startingmaterials in the process (e) according to the invention for preparingcompounds of the general formula (I). In the general formula (IX), Q¹,R¹ and R² preferably or in particular have those meanings which havealready been mentioned above, in connection with the description of thecompounds of the general formula (I) according to the invention, asbeing preferred or particularly preferred for Q¹, R¹ and R².

The starting materials of the general formula (IX) are known and/or canbe prepared by processes known per se.

The processes (a), (b), (c), (d) and (e) according to the invention forpreparing the novel compounds of the formula (I) are preferably carriedout using diluents. Suitable diluents are virtually all inert organicsolvents. These preferably include aliphatic and aromatic, optionallyhalogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane,petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylenechloride, ethylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether anddibutyl ether, glycol dimethyl ether and diglycol dimethyl ether,tetrahydrofaran and dioxane, ketones, such as acetone, methyl ethylketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, suchas methyl acetate and ethyl acetate, nitriles, such as, for example,acetonitrile and propionitrile, amides, such as, for example,dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and alsodimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide.

Reaction auxiliaries suitable for the processes (a), (b), (c), (d) and(e) according to the invention are all acid binders which arecustomarily used for such reactions.

Preference is given to alkali metal hydroxides, such as, for example,sodium hydroxide and potassium hydroxide, alkaline earth metalhydroxides, such as, for example, calcium hydroxide, alkali metalcarbonates and alkoxides, such as sodium carbonate and potassiumcarbonate, sodium tert-butoxide and potassium tert-butoxide, furthermorebasic nitrogen compounds, such as trimethylamine, triethylamine,tripropylamine, tributylamine, diisobutylamine, dicyclohexylaamine,ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine,N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN),1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and1,4-diazabicyclo[2.2.2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c), (d) and (e)according to the invention can be varied within a relatively wide range.In general, the processes are carried out at temperatures between −20°C. and +150° C., preferably at temperatures between 0° C. and +100° C.

The processes (a), (b), (c), (d) and (e) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to operate under elevated or reduced pressure.

For carrying out the processes (a), (b), (c), (d) and (e) according tothe invention, the starting materials required in each case aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess of one of the componentsused in each case. The reactions are generally carried out in a suitablediluent in the presence of an acid acceptor, and the reaction mixture isstirred for several hours at the temperature required in each case.Work-up in the processes (a), (b), (c), (d) and (e) according to theinvention is in each case carried out by customary methods (cf. thePreparation Examples).

If appropriate, salts can be prepared from the compounds of the generalformula (I) according to the invention. Such salts are obtained in asimple manner by customary methods for forming salts, for example bydissolving or dispersing a compound of the formula (I) in a suitablesolvent, such as, for example, methylene chloride, acetone, tert-butylmethyl ether or toluene, and adding a suitable base. The salts canthen—if appropriate after prolonged stirring—be isolated byconcentration or filtration with suction.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.Weeds in the broadest sense are to be understood as meaning all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

Depending on the concentration, the active compounds according to theinvention are suitable for total weed control, for example on industrialsites and rail tracks and on paths and areas with or without treegrowth. Equally, the compounds according to the invention can beemployed for controlling weeds in perennial crops, for example forests,ornamental tree plantings, orchards, vineyards, citrus groves, nutorchards, banana plantations, coffee plantations, tea plantations,rubber plantations, oil palm plantations, cocoa plantations, soft fruitplantings and hop fields, on lawns and turf and pastures and forselective weed control in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad activity spectrum when applied on thesoil and on above-ground parts of plants. To a certain extent, they arealso suitable for selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be used for controlling animal pestsand fungal or bacterial plant diseases. If appropriate, they can also beemployed as intermediates or precursors for the synthesis of furtheractive compounds.

According to the invention, it is possible to treat all plants and partsof plants. By plants are understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including transgenic plants and including plantvarieties which may or may not be protectable by plant variety propertyrights. Parts of plants are to be understood as meaning all above-groundand below-ground parts and organs of plants, such as shoot, leaf, flowerand root, examples which may be mentioned being leaves, needles, stems,trunks, flowers, fruit bodies, fruits and seeds and also roots, tubersand rhizomes. Plant parts also include harvested goods and vegetativeand generative propagation material, for example seedlings, tubers,rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterials, in particular in the case of seeds, furthermore by single- ormulti-layer coating.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspo-emulsion concentrates,natural and synthetic substances impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is to say liquid solventsand/or solid carriers, optionally with the use of surfactants, that isto say emulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Liquid solvents which are mainlysuitable are: aromatics, such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andwater.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks, such as calcite, marble, pumice, sepiolite, dolomite andsynthetic granules of inorganic and organic meals, and granules oforganic material, such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose, natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use dyestuffs, such as inorganic pigments, for exampleiron oxide, titanium oxide, Prussian blue, and organic dyestuffs, suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients, such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in the form of their formulations, can also be used asmixtures with known herbicides and/or with crop-plantcompatibility-improving substances (“safeners”), finished formulationsor tank mixes being possible. Also possible are mixtures withweed-killers comprising one or more known herbicides and a safener.

Possible components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron,anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamide,benazolin(-ethyl), benfuresate, bensulffuron(-methyl), bentazone,benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl),bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim,bromoxynil, butachlor, butafenacil(-allyl), butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim,clodinafop(-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalo-fop(-butyl),2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, dichloroprop(—P),diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide,diquat, dithiopyr, diuron, dymron, eproprodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop-(—P-ethyl), fentrazamide,flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, florasulam, fluazifop(—P-butyl), fluazolate,flucarbazone(-sodium), flufenacet, flufenpyr flumetsulam,flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam,fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam,flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl),fluridone, fluroxypyr(-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet(-methyl), fluthiamide, fomesafen, foramsulfuron,glufosinate(-ammonium), glyphosate-(-isopropylammonium), halosafen,haloxyfop(-ethoxyethyl-P-methyl), haloxy-fop(-ethoxyethyl, —P-methyl),hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic,imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl,-sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben,isoxachlortole, isoxaflutole, isoxapyrifop, ketospiradox, lactofen,lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione, metamitron,metazachlor, methabenzthiazuron, metobenzuron, metobromuron,(alpha-)metolachlor, metosulam, metoxuron, metribuzin,metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, penoxysulam, pentoxazone,pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor,primisulfuron(-methyl), profluazol, profoxydim, prometryn, propachlor,propanil, propaquizafop, propisochlor, propoxycarbazone(-sodium),propyzamide, prosulfocarb, prosulifuron, pyraflufen(-ethyl), pyrazogyl,pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim,pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac(-methyl),pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine,quizalofop(—P-ethyl), quizalofop(—P-tefuryl), rimsulfuron, sethoxydim,simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl),sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfiron(-methyl), andtriflusulfuron.

Furthermore suitable for the mixtures are known safeners, for example

AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D,DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole,fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (—P),mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing, scattering.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingcertain properties (“traits”) and which have been obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.They can be cultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention—also in combination with other agro-chemical activecompounds—, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably treated according to the inventioninclude all plants which, in the genetic modification, received geneticmaterial which imparted particularly advantageous useful properties(“traits”) to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapes), and particular emphasis is given to maize, soya beans,potatoes, cotton and oilseed rape. Traits that are emphasized are inparticular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds, forexample imidazolinones, sulphonylureas, glyphosate or phosphinotricin(for example the “PAT” gene). The genes which impart the desired traitsin question can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylurea, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these genetic traits orgenetic traits still to be developed, which plants will be developedand/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention,where in addition to the good control of weed plants, the abovementionedsynergistic effects with the transgenic plants or plant cultivars occur.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The following examples show the preparation and use of the activecompounds according to the invention:

PREPARATION EXAMPLES Example 1

0.45 g (2.19 mmol) of5-methoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-oneis dissolved in 50 ml of acetonitrile and, at room temperature (about20° C.), mixed with stirring, a little at a time, with 0.60 g (2.41mmol) of 4-ethoxycarbonyl-2-methyl-thiophene-3-sulfonamide and with 0.37g (2.41 mmol) of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU). Thereaction mixture is stirred at room temperature for 12 hours and thenconcentrated under reduced pressure. The residue is taken up inmethylene chloride and washed successively with IN hydrochloric acid andwith water, dried with sodium sulphate and filtered. The filtrate isconcentrated under reduced pressure, the residue is digested withisopropanol and the resulting crystalline product is isolated byfiltration with suction.

This gives 0.60 g (68% of theory) of ethyl4-[[[(3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylateas a pale yellow solid of melting point 176° C.

The sodium salt of the compound prepared according to Example 1 can beprepared, for example, as follows:

1.0 g (2.5 mmol) of ethyl4-[[[(3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylateare taken up in 25 ml of methylene chloride, and 0.10 g (2.5 mmol) ofsodium hydroxide (micropellets) are added. The mixture is stirred atroom temperature (or 20° C.) for 15 hours. The crystalline product isthen isolated by filtration with suction.

This gives 1.0 g of ethyl4-[[[(3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylatesodium salt of melting point 220° C.

Aanlogously to Example 1, and in accordance with the general descriptionof the preparation process according to the invention, it is alsopossible to prepare, for example, the compounds of the general formula(I) listed in table 1 below.

TABLE 1 (I)

Examples of the compounds of the formula (I) Ex. Melting No. Q¹ Q² R¹ R²R³ R⁴ point (° C.) 2 O O CH₃ CH₃ OCH₃ CH₃ 229 (Na-Salz) 3 O O CH₃ CH₃R³+R⁴: 204 —S(CH₂)₂— 4 O O CH₃ CH₃ R³+R⁴: 225 —O(CH₂)₂— 5 O O CH₃ CH₃R³+R⁴: 182 —S(CH₂)₃— 6 O O CH₃ CH₃ R³+R⁴: 239 —O(CH₂)₃— 7 O O CH₃ CH₃R³+R⁴: 219 —N(CH₃) —(CH₂)₃— 8 O O CH₃ CH₃

CH₃ 163 9 O O CH₃ CH₃

CH₃ 170 10 O O CH₃ CH₃

CH₃ 154 11 O O CH₃ CH₃

CH₃ 165 12 O O CH₃ CH₃ R³+R⁴: 220 —OCH₂—C(CH₃)₂—CH₂— 13 O O CH₃ CH₃

CH₃ 203 14 O O CH₃ CH₃

CH₃ 143 15 O O CH₃ CH₃ C₃H₇-n CH₃ 154 16 O O CH₃ CH₃ C₃H₇-i CH₃ 155 17 OO CH₃ CH₃ C₄H₉-s CH₃ 156 18 O O CH₃ CH₃ CH₂OCH₃ CH₃ 157 19 O O CH₃ CH₃

CH₃ 114 20 O O CH₃ CH₃ SC₂H₅ CH₃ 162 21 O O CH₃ CH₃ C₄H₉-t CH₃  99 22 OO CH₃ CH₃

CH₃ 180 23 O O CH₃ CH₃ CH₃ C₂H₅ 117 24 O O CH₃ CH₃

C₃H₇-n 151 25 O O CH₃ CH₃ C₂H₅ C₂H₅ 147 26 O O CH₃ CH₃ C₃H₇-n C₂H₅ 14628 O O CH₃ CH₃

C₂H₅ 150 29 O O CH₃ CH₃ CH₃ C₃H₇-n 135 30 O O CH₃ CH₃ CH₃ C₃H₇-i 147 31O O CH₃ CH₃ C₂H₅ C₃H₇-n 159 32 O O CH₃ CH₃ C₂H₅ C₃H₇-i 142 33 O O CH₃CH₃ C₃H₇-n C₃H₇-n 103 34 O O CH₃ CH₃ C₃H₇-i C₃H₇-n 116 35 O O CH₃ CH₃C₃H₇-i C₃H₇-i 121 36 O O CH₃ CH₃

C₃H₇-i 126 37 O O CH₃ CH₃ C₃H₇-n C₃H₇-i 120 38 O O CH₃ CH₃ OC₂H₅ C₂H₅124 39 O O CH₃ CH₃ C₂H₅ OC₂H₅ 183 40 O O CH₃ CH₃ Br CH₃ 189 41 O O CH₃CH₃ OCH₂CF₃ CH₃ 197 42 O O CH₃ CH₃ C₃H₇-n OCH₃ 106 43 O O CH₃ CH₃OCH₂CF₃

117 44 O O CH₃ CH₃ Br

166 45 O O CH₃ CH₃ CH₂OCH₃

185 46 O O CH₃ CH₃ CH₃

206 47 O O CH₃ CH₃ C₂H₅

175 48 O O CH₃ CH₃ C₃H₇-n

149 49 O O CH₃ CH₃ C₃H₇-i

214 50 O O CH₃ CH₃ C₄H₉-t

175 51 O O CH₃ CH₃ C₄H₉-s

205 52 O O CH₃ CH₃ H

201 53 O O CH₃ CH₃ H CH₃ 170 54 O O CH₃ CH₃ CH₃ N(CH₃)₂ 166 55 O O C₂H₅CH₃ OC₂H₅ CH₃ 172 56 O O C₂H₅ CH₃ OCH₃

173 57 S O CH₃ CH₃ OCH₃ CH₃ 159 58 S O CH₃ CH₃ OC₂H₅ CH₃ 133 59 S O CH₃CH₃ OC₃H₇-n CH₃  60 60 S O CH₃ CH₃ OC₃H₇-i CH₃ 182 61 S O CH₃ CH₃ OCH₃

201 62 S O CH₃ CH₃ OC₂H₅

181 63 S O CH₃ CH₃ OC₃H₇-n

137 64 S O CH₃ CH₃

127 65 S O CH₃ CH₃ CH₃ CH₃ 147 66 S O CH₃ CH₃ C₂H₅ CH₃ 117 67 S O CH₃CH₃ SCH₃ CH₃ 138 68 O O C₃H₇-i CH₃ OCH₃ CH₃ 190 69 O O C₃H₇-i CH₃ OC₂H₅CH₃ 193 70 O O C₃H₇-i CH₃ OC₃H₇-n CH₃ 189 71 O O C₃H₇-i CH₃ OC₃H₇-i CH₃184 72 O O C₃H₇-i CH₃ OCH₃

189 73 O O C₃H₇-i CH₃ OC₂H₅

115 74 O O C₃H₇-i CH₃ OC₃H₇-n

127 75 O O C₃H₇-i CH₃ OC₃H₇-i

251 76 O O C₃H₇-i CH₃

117 77 O O C₃H₇-i CH₃ SCH₃ CH₃ 185 78 O O C₃H₇-n CH₃ OCH₃ CH₃ 161 79 O OC₃H₇-n CH₃ OC₂H₅ CH₃  95 80 O O C₃H₇-n CH₃ OC₃H₇-n CH₃ 156 81 O O C₃H₇-nCH₃ OC₃H₇-i CH₃ 197 82 O O C₃H₇-n CH₃ OCH₃

169 83 O O C₃H₇-n CH₃ OC₂H₅

150 84 O O C₃H₇-n CH₃ OC₃H₇-n

 88 85 O O C₃H₇-n CH₃ OC₃H₇-i

 95 86 O O C₃H₇-n CH₃

192 87 O O C₃H₇-n CH₃ C₂H₅ CH₃ 110 88 O O C₃H₇-n CH₃ SCH₃ CH₃ 188 89 O OC₃H₇-i CH₃ R³ + R⁴: 194 —S(CH₂)₂— 90 O O C₃H₇-i CH₃ R³ + R⁴: 188—O(CH₂)₂— 91 O O C₃H₇-i CH₃ CH₂OCH₃ CH₃ 122 92 O O C₃H₇-i CH₃ R³ + R⁴:205 —OCH₂—C(CH₃)₂—CH₂— 93 O O C₃H₇-i CH₃

CH₃ 183 94 O O C₃H₇-i CH₃

CH₃  54 95 O O C₃H₇-i CH₃

CH₃ 159 96 O O C₃H₇-i CH₃

CH₃ 208 97 O O C₃H₇-i CH₃

CH₃ 115 98 O O C₃H₇-i CH₃ C₃H₇-n CH₃ 105 99 O O C₃H₇-i CH₃ C₃H₇-i CH₃106 100 O O C₃H₇-i CH₃ C₄H₉-s CH₃ 103 101 O O C₃H₇-i CH₃ SC₂H₅ CH₃ 113102 O O C₃H₇-i CH₃ C₄H₉-t CH₃ 131 103 O O C₃H₇-i CH₃

CH₃ 159 104 O O C₃H₇-i CH₃ CH₃ C₃H₇-i 165 105 S O C₃H₇-i CH₃ OCH₃ CH₃145 106 S O C₃H₇-i CH₃ OC₂H₅ CH₃ 175 107 S O C₃H₇-i CH₃ OC₃H₇-n CH₃ 166108 S O C₃H₇-i CH₃ OC₃H₇-i CH₃ 168 109 S O C₃H₇-i CH₃ OCH₃

137 110 S O C₃H₇-i CH₃ OC₂H₅

150 111 S O C₃H₇-i CH₃ OC₃H₇-n

136 112 S O C₃H₇-n CH₃ OCH₃ CH₃ 137 113 S O C₃H₇-n CH₃ OC₂H₅ CH₃ 160 114S O C₃H₇-n CH₃ OC₃H₇-n CH₃ 160 115 O O C₃H₇-i CH₃ OC₂H₅ C₂H₅ 123 116 O OC₃H₇-i CH₃ C₂H₅ OC₂H₅ 132 117 O O C₃H₇-i CH₃ OCH₂CF₃ CH₃ 188 118 O OC₃H₇-i CH₃ C₃H₇-n OCH₃ 245 119 O O C₃H₇-i CH₃ OCH₂CF₃

255 120 O O C₃H₇-i CH₃ CH₂OCH₃

164 121 S O C₃H₇-n CH₃ OC₃H₇-i CH₃ 172 122 S O C₃H₇-n CH₃ OCH₃

140 123 S O C₃H₇-n CH₃ OC₂H₅

139 124 S O C₃H₇-n CH₃ OC₃H₇-n

219 125 S O C₃H₇-n CH₃ OC₃H₇-i

120 126 S O CH₃ CH₃ OC₃H₇-i

144 127 O O C₃H₇-i CH₃ Br

156 128 O O C₃H₇-i CH₃ C₂H₅

143 129 O O C₃H₇-i CH₃ C₃H₇-i

160 130 O O C₃H₇-i CH₃ H

183 131 O O C₃H₇-i CH₃ H CH₃ 167 132 S O C₂H₅ CH₃ OCH₃ CH₃ 165 133 S OC₂H₅ CH₃ OC₂H₅ CH₃ 158 134 S O C₂H₅ CH₃ OC₃H₇-n CH₃ 150 135 S O C₂H₅ CH₃OC₃H₇-i CH₃ 176 136 S O C₂H₅ CH₃ OCH₃

159 137 S O C₂H₅ CH₃ OC₂H₅

162 138 S O C₂H₅ CH₃ OC₃H₇-n

156 139 S O C₂H₅ CH₃ OC₃H₇-i

135 140 O O C₂H₅ CH₃ R³ + R⁴: 189 —S(CH₂)₂— 141 O O C₂H₅ CH₃ R³ + R⁴:181 —S(CH₂)₃— 142 O O C₂H₅ CH₃ R³ + R⁴: 212 —OCH₂—C(CH₃)₂—CH₂— 143 O OC₂H₅ CH₃

CH₃ 174 144 O O C₂H₅ CH₃ CH₂OCH₃ CH₃ 116 145 O O C₂H₅ CH₃

CH₃ 131 146 O O C₂H₅ CH₃

CH₃ 171 147 O O C₂H₅ CH₃

CH₃ 210 148 O O C₂H₅ CH₃ C₃H₇-i CH₃ 175 149 O O C₂H₅ CH₃ SC₂H₅ CH₃ 131150 O O C₂H₅ CH₃ C₄H₉-t CH₃ 129 151 O O C₂H₅ CH₃

CH₃ 195 152 O O C₂H₅ CH₃ CH₃ C₂H₅ 140 153 O O C₂H₅ CH₃

C₃H₇-n 118 154 O O C₂H₅ CH₃ C₂H₅ C₂H₅ 117 155 O O C₂H₅ CH₃ C₃H₇-n C₂H₅165 156 O O C₂H₅ CH₃ C₃H₇-i C₂H₅ 136 157 O O C₂H₅ CH₃

C₂H₅ 148 158 O O C₂H₅ CH₃ CH₃ C₃H₇-n 135 159 O O C₂H₅ CH₃ CH₃ C₃H₇-i 135160 O O C₂H₅ CH₃ C₂H₅ C₃H₇-i 142 161 O O C₂H₅ CH₃

C₃H₇-i 147 162 O O C₂H₅ CH₃ OC₂H₅ C₂H₅ 127 163 O O C₂H₅ CH₃ C₂H₅ OC₂H₅145 164 O O C₂H₅ CH₃ OCH₂CF₃ CH₃ 175 165 O O C₂H₅ CH₃ C₃H₇-n OCH₃ 112166 O O C₂H₅ CH₃ OCH₂CF₃

147 167 O O C₂H₅ CH₃ CH₂OCH₃

147 168 O O C₂H₅ CH₃ CH₃

152 169 O O C₂H₅ CH₃ C₂H₅

159 170 O O C₂H₅ CH₃ C₃H₇-n

129 171 O O C₂H₅ CH₃ C₃H₇-i

158 172 O O C₂H₅ CH₃ C₄H₉-t

164 173 O O C₂H₅ CH₃ C₄H₉-s

149 174 O O C₂H₅ CH₃ H

184 175 O O C₂H₅ CH₃ H CH₃ 170 176 O O C₂H₅ CH₃ CH₃ N(CH₃)₂ 130 177 O OC₂H₅ CH₃ C₄H₉-i

147 178 O O C₂H₅ CH₃ C₄H₉-n

123 179 O O C₃H₇-n CH₃ R³ + R⁴: 182 —S(CH₂)₂— 180 O O C₃H₇-n CH₃ R³ +R⁴: 198 —S(CH₂)₃— 181 O O C₃H₇-n CH₃

CH₃ 153 182 O O C₃H₇-n CH₃

CH₃ 145 183 O O C₃H₇-n CH₃

CH₃ 183 184 O O C₃H₇-n CH₃

CH₃ 170 185 O O C₃H₇-n CH₃ C₃H₇-n CH₃ 127 186 O O C₃H₇-n CH₃ C₃H₇-i CH₃132 187 O O C₃H₇-n CH₃ C₄H₉-s CH₃ 125 188 O O C₃H₇-n CH₃ CH₂OCH₃ CH₃ 110189 O O C₃H₇-n CH₃ SC₂H₅ CH₃ 142 190 O O C₃H₇-n CH₃ CH₃ CH₃ 145 191 O OC₃H₇-n CH₃ CH₃ C₃H₇-i 174 192 O O C₃H₇-n CH₃ C₂H₅ C₃H₇-i 120 193 O OC₃H₇-n CH₃ OC₂H₅ C₂H₅ 121 194 O O C₃H₇-n CH₃ C₂H₅ OC₂H₅ 120 195 O OC₃H₇-n CH₃ OCH₂CF₃ CH₃ 140 196 O O C₃H₇-n CH₃ C₃H₇-n OCH₃ 112 197 O OC₃H₇-n CH₃ OCH₂CF₃

122 198 O O C₃H₇-n CH₃ CH₂OCH₃

117 199 O O C₃H₇-n CH₃ C₂H₅

180 200 O O C₃H₇-n CH₃ C₃H₇-i

183 201 O O C₃H₇-n CH₃ H

197 202 O O C₃H₇-n CH₃ H CH₃ 125 203 O O C₂H₅ CH₃ OC₃H₇-n CH₃ 139 204 OO C₂H₅ CH₃ OC₃H₇-i CH₃ 180 205 O O C₂H₅ CH₃ OC₂H₅

140 206 O O C₂H₅ CH₃ OC₃H₇-n

145 207 O O C₂H₅ CH₃ OC₃H₇-i

160 208 O O C₂H₅ CH₃

171 209 O O C₂H₅ CH₃ CH₃ CH₃ 155 210 O O C₂H₅ CH₃ C₂H₅ CH₃ 107 211 O OC₂H₅ CH₃ SCH₃ CH₃ 156 212 O O C₃H₇-i CH₃ C₂H₅ C₃H₇-i 251 213 O O CH₃C₂H₅ OC₃H₇-i

152 214 O O CH₃ C₂H₅ SC₂H₅ CH₃ 145 215 O O CH₃ C₂H₅ OC₂H₅ C₂H₅ 138 216 OO CH₃ C₂H₅ C₂H₅ OC₂H₅ 141 217 O O CH₃ C₂H₅ OCH₂CF₃ CH₃ 163 218 O O CH₃C₂H₅ C₃H₇-n OCH₃ 105 219 O O CH₃ C₂H₅ OCH₂CF₃

161 220 O O CH₃ CH₃ OCH₃ CH₃ 146 (Triethyl- ammonium salt) 221 O O CH₃C₂H₅ OCH₃ CH₃ 236 (Lithium salt) 222 O O CH₃ C₂H₅ OCH₃ CH₃ 154(Triethyl- ammonium salt) 223 O O CH₃ C₂H₅ OCH₃ CH₃ 162 (N,N-di-methylpyridin- 4-yl- ammonium salt) 224 O O CH₃ C₂H₅ OCH₃ CH₃ 150(1-hydroxy- methyl- propyl- propyl- ammonium salt) 225 O O CH₃ CH₃ OCH₃CH₃ 151 (Diethyl- ammonium salt) 226 O O CH₃ CH₃ OCH₃ CH₃ 115 (Pyrroli-dinium salt) 227 O O CH₃ CH₃ OCH₃ CH₃ 159 (1-hydroxy- methyl- propyl-ammonium salt)

Use Examples

In the use examples, the following prior-art compounds (all known fromWO-A-01/05788) are used for comparison:

-   methyl    4-[[[(4,5-dihydro4-methyl-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate    (A)

-   methyl    4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-n-propoxy-1H-1,2,4-triazol-1-yl)-carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate    (B)

-   methyl    4-[[[(4-cyclopropyl-4,5-dihydro-5-oxo-3-isopropoxy-1H-1,2,4-triazol-1-yl)-carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate    (C)

-   methyl    4-[[[(3,4-dicyclopropyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate    (D)

-   methyl    4-[[[(4,5-dihydro-3,4-dimethyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate    (E)

-   methyl    4-[[[(4,5-dihydro-3-ethyl-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)    carbonyl]-amino]sulfonyl]-5-methyl-3-thiophenecarboxylate (F)

-   methyl    4-[[[(4,5-dihydro-4-methyl-3-methylthio-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl]amino]sulfonyl]-5-methyl-3-thiophenecarboxylate    (G)

Example A

Post-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compounddesired are applied per unit area. The concentration of the spray liquoris chosen such that the particular amounts of active compound desiredare applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 15,18, 20, 22, 39, 42, 45, 46, 47, 48, 55 and 56 show a considerablystronger activity against weeds and a substantially better compatibilitywith crop plants such as, for example, maize, oilseed rape and wheatthan the known compounds (A) and (B).

Example B

Pre-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concetrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, thesoil is sprayed with the preparation of active compound such that theparticular amount of active compound desired is applied per unit area.The concentration of active compound in the spray liquor is chosen suchthat the particular amount of active compound desired is applied in 1000litres of water per hectare.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

In this test, for example, the compounds of Preparation Examples 1, 15,18, 20, 22, 38, 39, 41, 42, 43, 45, 46, 47, 48, 55 and 56 exhibitconsiderably stronger activity against weeds than the known compounds(A), (B), (C), (D), (E), (F) and (G), and substantially, they aretolerated well by crop plants, such as, for example, maize, soyabean andwheat.

TABLE A1 Post-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) wheat fatua BromusEchinochloa Lolium Datura Viola Xanthium (B) 15 30 50 50 — 60 80 — 50(A) 15 0 30 50 60 30 50 30 70 (56) 15 0 90 90 95 90 90 95 95

TABLE A2 Post-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) maize Alopecurus BromusEchinochloa Lolium Datura Polygonum Xanthium (B) 15 90 0 50 — 60 80 7050 (A) 15 30 70 50 60 30 50 50 70 (55) 15 0 90 90 90 90 95 90 95

TABLE A3 Post-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) wheat maize Echinochloa LoliumDatura Polygonum Viola Xanthium (B) 15 30 90 — 60 80 70 — 50 (A) 15 0 3060 30 50 50 30 70 (1) 15 0 0 90 90 95 95 95 95

TABLE A4 Post-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) wheat maize Alopecurus fatuaBromus Digitaria Setaria (B) 15 30 90 0 50 50 20 60 (A) 15 0 30 70 30 5010 30 (22) 15 0 0 99 80 95 95 90

TABLE A5 Post-emergence-Test/greenhouse Com- pound of Prep- appli-aration cation Example rate No. (gai/ha) wheat Alopecurus BromusEchinochloa Viola (B) 15 30 0 50 — — (A) 15 0 70 50 60 30 (20) 15 0 9080 100 100

TABLE A6 Post-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) maize Alopecurus fatuaBromus Digitaria Echinochloa Lolium Setaria (B) 15 90 0 50 50 20 — 60 60(A) 15 30 70 30 50 10 60 30 30 (18) 15 0 95 95 80 95 95 95 100

TABLE A7 Post-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) Alopecurus fatua BromusDigitaria Echinochloa Lolium Setaria (B) 15 0 50 50 20 — 60 60 (A) 15 7030 50 10 60 30 30 (15) 15 95 90 80 100 90 80 90

TABLE A8 Post-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) fatua Bromus DigitariaEchinochloa Lolium Setaria (A) 15 30 50 10 60 30 30 (39) 15 90 95 95 10095 95 (45) 15 90 90 100 100 95 90

TABLE A9 Post-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) rape Alopecurus Echinochloa LoliumChenopodium (A) 15 95 70 60 30 80 (42) 15 0 90 90 90 95

TABLE A10 Post-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) fatua Digitaria EchinochloaLolium Setaria Viola Xanthium (A) 15 30 10 60 30 30 30 70 (47) 15 95 9095 100 90 100 — (48) 15 90 90 95 100 80 95 90

TABLE A11 Post-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) fatua Bromus DigitariaLolium Setaria Xanthium (B) 15 50 50 20 60 60 50 (39) 15 90 95 95 95 95— (45) 15 90 90 100 95 90 — (47) 15 95 80 90 100 90 80

TABLE A12 Post-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) Alopecurus Avena fatua DigitariaLolium Xanthium (B) 15 0 50 20 60 50 (46) 15 80 80 90 95 — (48) 15 — 9090 100 90

TABLE B1 Pre-emergence-Test/greenhouse Compound of Preparation ExampleNo. application rate (gai/ha) wheat maize Bromus Lolium AmaranthusMatricaria Solanum Stellaria Xanthium (G) 15 0 0 — 60 40 70 80 80 40 (F)15 0 0 70 40 40 20 80 70 0 (E) 15 0 0 20 0 10 20 70 40 0 (D) 15 0 20 1020 80 10 80 60 0 (C) 15 0 0 70 50 80 80 — 80 0 (B) 15 0 0 40 20 80 40 8060 0 (A) 15 0 0 60 0 — 50 80 80 0 (56) 15 0 0 95 95 100 100 100 100 95(1) 15 0 0 95 90 100 100 100 100 95

TABLE B2 Pre-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) wheat maize soybeans AlopecurusLolium Amaranthus Matricaria Solanum Stellaria (G) 15 0 0 50 — 60 40 7080 80 (F) 15 0 0 10 70 40 40 20 80 70 (E) 15 0 0 0 20 0 10 20 70 40 (D)15 0 20 0 0 20 80 10 80 60 (C) 15 0 0 0 0 50 80 80 — 80 (B) 15 0 0 0 2020 80 40 80 60 (A) 15 0 0 0 60 0 — 50 80 80 (20) 15 0 0 0 90 95 95 100100 100

TABLE B3 Pre-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) wheat maize Alopecurus BromusLolium Polygonum Solanum Stellaria Xanthium (G) 15 0 0 — — 60 — 80 80 40(F) 15 0 0 70 70 40 50 80 70 0 (E) 15 0 0 20 20 0 20 70 40 0 (D) 15 0 200 10 20 10 80 60 0 (C) 15 0 0 0 70 50 60 — 80 0 (B) 15 0 0 20 40 20 5080 60 0 (A) 15 0 0 60 60 0 0 80 80 0 (55) 15 0 0 95 95 90 95 100 100 95(22) 15 0 0 95 100 95 95 100 100 — (15) 15 0 0 100 90 95 90 95 100 95

TABLE B4 Pre-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) wheat maize soybeans AlopecurusSetaria Amaranthus Matricaria Stellaria (G) 15 0 0 50 — 70 40 70 80 (F)15 0 0 10 70 30 40 20 70 (E) 15 0 0 0 20 20 10 20 40 (D) 15 0 20 0 0 1080 10 60 (C) 15 0 0 0 0 50 80 80 80 (B) 15 0 0 0 20 40 80 40 60 (A) 15 00 0 60 0 — 50 80 (18) 15 0 0 0 95 95 95 100 95

TABLE B5 Pre-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) maize soybeans Lolium SetariaAmaranthus Chenopodium Solanum Stellaria (G) 15 0 50 60 70 40 50 80 80(F) 15 0 10 40 30 40 0 80 70 (E) 15 0 0 0 20 10 0 70 40 (D) 15 20 0 2010 80 0 80 60 (C) 15 0 0 50 50 80 40 — 80 (B) 15 0 0 20 40 80 40 80 60(A) 15 0 0 0 0 — 50 80 80 (38) 15 0 0 80 95 100 95 100 100

TABLE B6 Pre-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) wheat maize Alopecurus SetariaAmaranthus Chenopodium Solanum Stellaria (G) 15 0 0 — 70 40 50 80 80 (F)15 0 0 70 30 40 0 80 70 (E) 15 0 0 20 20 10 0 70 40 (D) 15 0 20 0 10 800 80 60 (C) 15 0 0 0 50 80 40 — 80 (B) 15 0 0 20 40 80 40 80 60 (A) 15 00 60 0 — 50 80 80 (41) 15 0 0 100 95 100 100 100 100

TABLE B7 Pre-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) wheat Digitaria Lolium SetariaAmaranthus Solanum Stellaria (G) 15 0 50 60 70 40 80 80 (F) 15 0 60 4030 40 80 70 (E) 15 0 0 0 20 10 70 40 (D) 15 0 20 20 10 80 80 60 (C) 15 020 50 50 80 — 80 (B) 15 0 0 20 40 80 80 60 (A) 15 0 0 0 0 — 80 80 (39)15 0 100 95 100 100 95 100

TABLE B8 Pre-emergence-Test/greenhouse Compound of Preparationapplication Example No. rate (gai/ha) wheat maize soybeans AlopecurusLolium Matricaria Stellaria (G) 15 0 0 50 — 60 70 80 (F) 15 0 0 10 70 4020 70 (E) 15 0 0 0 20 0 20 40 (D) 15 0 20 0 0 20 10 60 (C) 15 0 0 0 0 5080 80 (B) 15 0 0 0 20 20 40 60 (A) 15 0 0 0 60 0 50 80 (46) 15 50 0 0 9590 100 100

TABLE B9 Pre-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) fatua Lolium SetariaAmaranthus Matricaria Polygonum Stellaria (G) 15 50 60 70 40 70 70 80(F) 15 60 40 30 40 20 50 70 (E) 15 0 0 20 10 20 20 40 (D) 15 70 20 10 8010 10 60 (C) 15 50 50 50 80 80 60 80 (B) 15 10 20 40 80 40 50 60 (A) 150 0 0 — 50 0 80 (43) 15 — 95 95 100 100 100 100 (45) 15 95 100 100 100100 95 100 (47) 15 95 80 95 100 100 90 100 (48) 15 95 95 — 100 95 95 100

TABLE B10 Pre-emergence-Test/greenhouse Compound of Preparationapplication Avena Example No. rate (gai/ha) fatua Bromus Lolium SetariaAmaranthus Galium Stellaria (G) 15 50 — 60 70 40 30 80 (F) 15 60 70 4030 40 10 70 (E) 15 0 20 0 20 10 0 40 (D) 15 70 10 20 10 80 0 60 (C) 1550 70 50 50 80 70 80 (B) 15 10 40 20 40 80 20 60 (A) 15 0 60 0 0 — 10 80(42) 15 90 95 95 95 100 100 100

1. A compound of formula (I)

or salts thereof, in which Q¹ represents O, Q² represents O, R¹represents optionally cyano-, halogen-, or C₁-C₄-alkoxy-substitutedalkyl having 1 to 6 carbon atoms; represents optionally cyano- orhalogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbonatoms; or represents optionally cyano-, halogen-, orC₁-C₄-alkyl-substituted cycloalkyl or cycloalkylalkyl having in eachcase 3 to 6 carbon atoms in the cycloalkyl group and, optionally, 1 to 4carbon atoms in the alkyl moiety, R² represents hydrogen, cyano, nitro,or halogen; represents optionally cyano-, halogen-, orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulfinyl, or alkylsulfonyl having in each case 1 to 6 carbon atomsin the alkyl group; or represents optionally cyano- orhalogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyloxy havingin each case 2 to 6 carbon atoms in the alkenyl or alkynyl group, R³represents halogen-substituted alkoxy having 1 to 6 carbon atoms, and R⁴represents hydrogen, hydroxy, amino, or cyano; representsC₂-C₁₀-alkylideneamino; represents optionally fluorine-, chlorine-,bromine-, cyano-, C₁-C₄-alkoxy-, C₁ -C₄-alkyl-carbonyl-, orC₁-C₄-alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms;represents optionally fluorine-, chlorine-, and/or bromine-substitutedalkenyl or alkynyl having in each case 2 to 6 carbon atoms; representsoptionally fluorine-, chlorine-, bromine-, cyano-, C₁-C₄-alkoxy-, orC₁-C₄-alkoxy-carbonyl-substituted alkoxy, alkylamino oralkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkylgroups; represents alkenyloxy having 3 to 6 carbon atoms; representsdialkylamino having in each case 1 to 4 carbon atoms in the alkylgroups;or represents optionally fluorine-, chlorine-, bromine-, cyano-,and/or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkylamino, orcycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkylgroup and, optionally, 1 to 4 carbon atoms in the alkyl moiety.
 2. Acompound according to claim 1 in which R¹ represents optionally cyano-,fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n-or isoproyl, or n-, iso-, s-, or t-butyl; represents optionally cyano-,fluorine-, or chlorine-substituted propenyl, butenyl, propynyl, orbutynyl; represents optionally cyano-, fluorine-, chlorine-, methyl-, orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, orcyclohexylmethyl, R² represents hydrogen, cyano, fluorine, chlorine, orbromine; represents optionally cyano-, fluorine-i chlorine-, methoxy-,or ethoxy-substituted methyl, ethyl, n- or isopropyl, n-, iso-, s-, ort-butyl, methoxy, ethoxy, n- or isopropoxy, methoxycarbonyl,ethoxycarbonyl, n- or isopropoxycarbonyl, methylthio, ethylthio, n- orisopropylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, orethylsulfonyl; or represents optionally cyano-, fluorine-, orchlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy,butenyloxy, propynyloxy, or butynyloxy, R³ represents fluorine- orchlorine-substituted methoxy, ethoxy, n- or isopropoxy, n-, iso-, s- ort-butoxy, n-, iso-, s-, or t-pentyloxy, or neopentyloxy, and R⁴represents hydrogen, hydroxy, or amino; represents optionally fluorine-,chlorine-, cyano-, methoxy-, or ethoxy-substituted methyl, ethyl, n- orisopropyl, or n-, iso-, s-, or t-butyl; represents optionally fluorine-,chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl,propynyl, or butynyl; represents optionally fluorine-, chlorine-,cyano-, methoxy-, or ethoxy-substituted methoxy, ethoxy, n- orisopropoxy, n-, iso-, s-, or t-butoxy, methylamino, ethylamino, n- orisopropylamino, or n-, iso-, s-, or t-butylamino; represents propenyloxyor butenyloxy; represents dimethylamino or diethyl-amino; or representsoptionally fluorine-, chlorine-, methyl-, and/or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino,cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl,cyclobutyl methyl, cyclopentyl methyl, or cyclohexylmethyl.
 3. Acompound according to claim 1 in which R¹ represents optionallyfluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, orn- or isopropyl, R² represents fluorine, chlorine, or bromine; orrepresents optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, or n- or isopropyl, R³ representsfluorine- or chlorine-substituted methoxy, ethoxy, n- or isopropoxy, n-,iso-, s-, or t-butoxy, n-, iso-, s-, or t-pentyloxy, or neopentyloxy,and R⁴ represents optionally fluorine-, chlorine-, methoxy-, orethoxy-substituted methyl, ethyl, or n- or isopropyl; representsoptionally fluorine- or chlorine-substituted ethenyl, propenyl, orpropynyl; represents optionally fluorine-, chlorine-, methoxy-, orethoxy-substituted methoxy, ethoxy, or n- or isopropoxy; representsmethylamino; or represents cyclopropyl.
 4. A compound according to claim3 in which R¹ represents methyl.
 5. A compound according to claim 3 inwhich R¹ represents ethyl.
 6. A compound according to claim 3 in whichR¹ represents n-propyl.
 7. A compound according to claim 3 in which R¹represents isopropyl.
 8. A process for preparing a compound according toclaim 1 comprising (a) reacting a substituted thiophene-3-sulphonamideof formula (II)

in which R¹ and R² are as defined for formula (I) of claim 1, with asubstituted triazolinone of formula (III)

in which Q¹, Q², R³, and R⁴ are as defined for formula (I) of claim 1,and Z represents halogen, alkoxy, aryloxy, or arylalkoxy, optionally inthe presence of a reaction auxiliary and optionally in the presence of adiluent, or (b) reacting a substituted thiene-3-ylsulphonyliso(thio)cyanate of formula (IV)

in which Q¹, R¹, and R² are as defined for formula (I) of claim 1, witha triazolinone of formula (V)

in which Q², R⁴, and R⁵ are as defined for formula (I) of claim 1,optionally in the presence of a reaction auxiliary and optionally in thepresence of a diluent, or (c) reacting a substitutedthiophene-3-sulphonyl chloride of formula (VI)

in which R¹ and R² are as defined for formula (I) of claim 1, with atriazolinone of formula (V)

in which Q², R⁴ , and R⁵ are as defined for formula (I) of claim 1, anda metal cyanate of formula (VII)M-Q¹-CN  (VII) in which Q¹ is as defined for formula (I) of claim 1,optionally in the presence of a reaction auxiliary and optionally in thepresence of a diluent, or (d) reacting a substitutedthiophene-3-sulphonyl chloride of formula (VI)

in which R¹ and R² are as defined for formula (I) of claim 1, with atriazolinone carboxamide of formula (VIII)

in which Q¹, Q², R³, and R⁴ are as defined for formula (I) of claim 1,optionally in the presence of a reaction auxiliary and optionally in thepresence of a diluent, or (e) reacting a substitutedthiene-3-yl-sulphonylaminocarbonyl compound of formula (IX)

in which Q¹, R¹, and R² are as defined for formula (I) of claim 1, and Zrepresents halogen, alkoxy, aryloxy, or arylalkoxy, with a triazolinoneof formula (V)

in which Q², R⁴, and R⁵ are as defined for formula (I) of claim 1,optionally in the presence of a reaction auxiliary and optionally in thepresence of a diluent.
 9. A process according to claim 8 additionallycomprising converting a compound of formula (I) prepared according claim8 to a salt thereof.
 10. A herbicidal composition comprising a compoundaccording to claim 1 and one or more extenders and/or surfactants.
 11. Amethod for controlling unwanted vegetation comprising allowing aneffective amount of one or more compounds according to claim 1 to act onan unwanted plant and/or its habitat.
 12. A compound according to claim1 in which Q¹ represents O, Q² represents O, R¹ represents alkyl having1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, R²represents alkyl having 1 to 6 carbon atoms, R³ representshalogen-substituted alkoxy having 1 to 6 carbon atoms, and R⁴ representsalkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbonatoms.